Diethyl benzylphosphonate → HCID 9815603, compound

HRID 967739Notes

Reaction equation

HRID 967739 reaction equation
[H-].[Na+].[CH2:3](P(=O)(OCC)OCC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:18][C:19]1[S:20][CH:21]=[C:22]([CH:24]=O)[N:23]=1>COCCOC.C(OCC)(=O)C>[CH3:18][C:19]1[S:20][CH:21]=[C:22](/[CH:24]=[CH:3]/[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:23]=1

Participants

6

Reactant 3

HCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 27631912-Methyl-1,3-thiazole-4-carbaldehyde

Product 1

HCID 9815603HCID 9815603, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (120 mg of a 60% suspension in mineral oil, 3.0 mmol) was slurried in DME (6 mL) and cooled to 0° C. Diethyl benzylphosphonate (1.1 g, 5.0 mmol) was added dropwise and after 15 minutes, 2-methyl-1,3-thiazole-4-carbaldehyde (320 mg, 2.5 mmol) in DME (5 mL) was added dropwise to the reaction mixture. After 3 h at 0° C. the reaction mixture was diluted with ethyl acetate (10 mL) and washed with saturated aqueous NH4Cl (10 mL), saturated aqueous NaHCO3 (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with 90:10 hexane:ethyl acetate to afford 2-methyl-4-[(E)-2-phenylethenyl]-1,3-thiazole (330 mg, 65% yield) as an oil. 1H NMR (CDCl3, 300 MHz) δ 7–7.5 (m, 8H), 2.7 (s, 3H). MS (ESI) 202.1 (M++H).

Workup

  1. washwashed with saturated aqueous NH4Cl (10 mL), saturated aqueous NaHCO3 (10 mL), brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel eluting with 90:10 hexane

Sources & evidence

ORD record
ord-af1465c965b94c82a92e9e03a936ce04
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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